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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:03:11 UTC
Update Date2022-03-07 02:56:37 UTC
HMDB IDHMDB0040499
Secondary Accession Numbers
  • HMDB40499
Metabolite Identification
Common Name18alpha-Hydroxyglycyrrhetic acid
Description18alpha-Hydroxyglycyrrhetic acid, also known as 18α-hydroxyglycyrrhetate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a small amount of articles have been published on 18alpha-Hydroxyglycyrrhetic acid.
Structure
Data?1563863557
Synonyms
ValueSource
18a-HydroxyglycyrrhetateGenerator
18a-Hydroxyglycyrrhetic acidGenerator
18alpha-HydroxyglycyrrhetateGenerator
18Α-hydroxyglycyrrhetateGenerator
18Α-hydroxyglycyrrhetic acidGenerator
10,14b-Dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylateGenerator
Chemical FormulaC30H46O5
Average Molecular Weight486.6832
Monoisotopic Molecular Weight486.334524582
IUPAC Name10,14b-dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
Traditional Name10,14b-dihydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,3,4,5,6,7,8,8a,10,11,12,12b-dodecahydropicene-2-carboxylic acid
CAS Registry Number17991-67-2
SMILES
CC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O
InChI Identifier
InChI=1S/C30H46O5/c1-24(2)19-8-11-29(7)22(27(19,5)10-9-21(24)32)18(31)16-20-28(29,6)15-14-26(4)13-12-25(3,23(33)34)17-30(20,26)35/h16,19,21-22,32,35H,8-15,17H2,1-7H3,(H,33,34)
InChI KeyFCVHQYZUEPQNJU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point252 - 255 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.024 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0023 g/LALOGPS
logP4.54ALOGPS
logP5.03ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity135.64 m³·mol⁻¹ChemAxon
Polarizability56.19 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+211.95231661259
DarkChem[M-H]-202.59531661259
DeepCCS[M-2H]-243.44730932474
DeepCCS[M+Na]+218.88930932474
AllCCS[M+H]+218.432859911
AllCCS[M+H-H2O]+216.932859911
AllCCS[M+NH4]+219.832859911
AllCCS[M+Na]+220.232859911
AllCCS[M-H]-215.032859911
AllCCS[M+Na-2H]-217.332859911
AllCCS[M+HCOO]-219.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
18alpha-Hydroxyglycyrrhetic acidCC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O3880.8Standard polar33892256
18alpha-Hydroxyglycyrrhetic acidCC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O3522.9Standard non polar33892256
18alpha-Hydroxyglycyrrhetic acidCC1(C)C(O)CCC2(C)C1CCC1(C)C2C(=O)C=C2C1(C)CCC1(C)CCC(C)(CC21O)C(O)=O4092.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #1CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C14168.9Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #2CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C14146.3Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #3CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C14089.6Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,1TMS,isomer #4CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C14062.2Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C14093.1Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #2CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C14119.2Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #3CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C14044.7Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #4CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C14052.3Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #5CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C13988.9Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TMS,isomer #6CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C14003.6Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C13975.4Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #2CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O)C13937.3Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #3CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C13909.4Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TMS,isomer #4CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C13877.1Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,4TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C13805.6Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,4TMS,isomer #1CC1(C(=O)O[Si](C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C)C13735.5Standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #1CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C14376.4Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #2CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C14345.3Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #3CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C14321.5Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,1TBDMS,isomer #4CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C14300.9Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #1CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C14524.8Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #2CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C14539.4Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #3CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C14476.7Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #4CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C14486.0Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #5CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C14425.4Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,2TBDMS,isomer #6CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O)C14427.4Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #1CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C14596.5Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #2CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O)C14565.3Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #3CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C14535.7Semi standard non polar33892256
18alpha-Hydroxyglycyrrhetic acid,3TBDMS,isomer #4CC1(C(=O)O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3(C)C(=CC(O[Si](C)(C)C(C)(C)C)=C4C5(C)CCC(O)C(C)(C)C5CCC43C)C2(O[Si](C)(C)C(C)(C)C)C14470.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-0309800000-2bb054ebd2e623a3f47b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid GC-MS (2 TMS) - 70eV, Positivesplash10-014i-1040619000-dc37f95bb9980848f7372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Positive-QTOFsplash10-0gb9-0000900000-b759df6a4c6f6b9a2e952015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Positive-QTOFsplash10-0v4i-0010900000-ffaba9d09198c51ea2dd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Positive-QTOFsplash10-00xr-5352900000-ae971104cf608ea3ce102015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Negative-QTOFsplash10-000i-0000900000-20d08b5715a8fe73cbfc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Negative-QTOFsplash10-00y3-0000900000-4fa2009950b40dd6e1f02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Negative-QTOFsplash10-00ou-2001900000-ccc7d3c0f909b4769f192015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Positive-QTOFsplash10-000i-0000900000-54af6e1e651b319692d32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Positive-QTOFsplash10-01dr-0100900000-ba817cdf63a77b3dee2d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Positive-QTOFsplash10-014r-5985200000-4e784a68cfa44acdee752021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 10V, Negative-QTOFsplash10-000i-0000900000-6a75a140e72d68a6c1932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 20V, Negative-QTOFsplash10-000i-0000900000-bb75148d629eb4e4973a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 18alpha-Hydroxyglycyrrhetic acid 40V, Negative-QTOFsplash10-000i-0000900000-8c9b45ee368045fc119b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020262
KNApSAcK IDNot Available
Chemspider ID35014951
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14189465
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1883871
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.